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Interpretation:
The structures of the two enone products obtained, in the approximate ratio of 9:1, when 2, 5-heptanedione undergoes intramolecular aldol condensation in the presence of aqueous NaOH, are to be given.
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To give:
The structures of the two enone products obtained, in the approximate ratio of 9:1, when 2, 5-heptanedione undergoes intramolecular aldol condensation in the presence of aqueous NaOH.
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Chapter 23 Solutions
Organic Chemistry
- Acid-catalyzed hydrolysis of the following epoxide gives a trans diol. Of the two possible trans diols, only one is formed. How do you account for this stereoselectivity?arrow_forward2. Intramolecular aldol cyclization of 3,3-dimethyl-2,5-nonanedione with aqueous NaOH yields a mixture of two enone products in the approximate ratio 9:1. Write their structures and show how each is formed.arrow_forwardPropose a mechanism for the reaction of benzyl acetate with methylamine. Label theattacking nucleophile and the leaving group, and draw the transition state in which theleaving group leaves.arrow_forward
- The Stork reaction is a condensation reaction between an enamine donor and an α,β-unsaturated carbonyl acceptor. The overall reaction consists of a three-step sequence of formation of an enamine from a ketone, Michael addition to an α,β-unsaturated carbonyl compound, and hydrolysis of the enamine in dilute acid to regenerate the ketone. Consider the Stork reaction between acetophenone and 3-buten-2-one. Draw the structure of the product of the enamine formed between acetophenone and pyrrolidine. Draw the structure of the Michael addition product. Draw the structure of the final product.arrow_forward2-Ethyl-1-hexanol was needed for the synthesis of the sunscreen octyl p-methylcinnamate. Show how this alcohol could be synthesized (a) by an aldol condensation of butanal and (b) by a malonic ester synthesis starting with diethyl malonate.arrow_forwardThe intramolecular aldol reaction of 6-oxoheptanal [CH3CO(CH2)4CHO] can yield threecyclic D,E-unsaturated ketones. Give the threeproducts and suggest a mechanism for formingone of the products.arrow_forward
- The Robinson annulation is a combination of two carbonyl coupling reactions, the Michael reaction and the intramolecular aldol condensation. The most common partners in the reaction are a nucleophilic donor (such as a cyclic ketone, a β-keto ester, an enamine, or a β-diketone) and an α,β-unsaturated ketone acceptor. The product is a substituted 2-cyclohexenone derivative. Draw the structures of the nucleophilic β-keto ester and the α,β-unsaturated ketone acceptor that were combined in a Robinson annulation to give the following product: Draw the β-keto ester as an ethyl ester,arrow_forwardThe Robinson annulation is a combination of two carbonyl coupling reactions, the Michael reaction and the intramolecular aldol condensation. The most common partners in the reaction are a nucleophilic donor (such as a cyclic ketone, a β-keto ester, an enamine, or a β-diketone) and an α,β-unsaturated ketone acceptor. The product is a substituted 2-cyclohexenone derivative. Draw the structures of the nucleophilic β-diketone and the α,β-unsaturated ketone acceptor that were combined in a Robinson annulation to give the following product:arrow_forwardShow how to prepare a,b-unsaturated aldehyde by an aldol reaction followed by dehydration of the aldol product.arrow_forward
- The following is a key step in the synthesis of morphine involving the conversion of A to B. Draw a stepwise mechanism for this process, including an intramolecular alkylation and intramolecular aldol.A B A CHO SO2 Br N K2CO3 B N S02arrow_forwardQ/ Give the product for the following reactions: OH (1) Acetone + acetaldehyde OH (2)2 Acetone ? Q/ Give the mechanism of reactions (1) and (2). Q/ Give the mechanism of aldol condensation under the influence of dilute acid.arrow_forwardPropose a synthesis of the anti-inflammatory drug Fenclorac from phenylcyclohexane.arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
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